Kerrie Woodhouse

Whimsical Watercolour

Art Challenges - Pros, Cons and How to choose the best challenge for you

art tipsKerrie Woodhouse

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What is an art challenge?

Art challenges come in all sorts of shapes and sizes but generally involve a commitment on the part of an artist to complete some sort of series of work over a period of time. An art challenge can be a great way to for any artist to improve their skills, build a body of work and can even be a fairly social activity.

There are a lot of good things about art challenges, but let’s be honest - that is only half the story. 

Before diving into an art challenge you might want to consider these pros and cons of art challenges and how best to make an art challenge work for you.


Pros of art challenges

Art challenges reduce procrastination

There are so many decisions that every artist has to make in just one art piece. 

What subject to draw/paint?

What medium to use?

What surface to work on and in what size?

All of these choices are excellent procrastination fodder. Very often there is some sort of fear behind any hesitation. We worry that our work won’t be good enough, that our art is a waste of time and so on. Taking up an art challenge solves a lot of that. Essentially it gives you an assignment, with parameters and deadlines and purpose. 


Art challenges stimulate creativity

Once your challenge is defined you then find yourself in the position of being accountable. You have a piece of work to do and some sort of time frame.

If it is a daily challenge with prompts for example you have to make art whether you feel like it or not. Not when inspiration strikes, or you feel in the right sort of mood.

In short it makes you a bit more professional.

It also stimulates your creativity. What you find is that you actually can be creative on demand. You do have ideas, even when you think you don’t. Often it takes being forced into compulsory creating to realise just how creative you really are.


Art challenges are social and fun

Taking part in a big organised challenge, like World Watercolour Month or Inktober for example, can be a really fun social sort of thing to do. It can be really motivating seeing everyone else’s contributions and being a part of the community that forms around these challenges.

The bigger these challenges are the more buzz that tends to be created and that can put a little zing back into your art practice!

Art challenges increase productivity

Making a commitment to complete a challenge means by definition that you will be very productive. In a set time frame you will have completed a body of work. That can be a great way to build a portfolio. You also (having established that you can be creative on demand, see above!) realise just what you are capable of producing on a daily or weekly basis when you put your mind to it.

Art challenges develop your skills

Building a portfolio is not the only benefit of creating a body of work.

An art challenge can be an excellent way to develop  your skills. Practice makes perfect. Every piece of artwork you make makes you a better artist - even if you produce something you are not happy with.  It is all part of the process.

Setting the parameters of your challenge is a chance to identify what skills you might want to focus on. Perhaps it is really getting to grips with a particular medium, perhaps it is perspective drawing, perhaps linework.

It is the repetition that is the key. Whatever it is that you will be repeating during the challenge you are sure to get better at.

Cons of Art Challenges

So as you can see there is no shortage of good reasons to jump into an art challenge.

But before you do, there are some adverse consequences to consider to be fair to yourself.

Art challenges can be a substantial time commitment

An art challenge can become a substantial time commitment especially if you make it public. I will get back to that under what I call scope creep below, but do consider what may have to be given up to create the time for this art challenge.

Remember that if you are planning to share your challenge by posting it on social media this will mean not only the time you need to create the artwork, but the time you need to present it, eg photograph/scan the work, post with a caption, reply to the comments from all your adoring fans 😉comment on other artists posts if it is one of the big organised ones like Inktober.  


Art challenges can be demoralising and demotivating

If you do take your art challenge public and it is one of the big organised ones, it can become something of a comparison game.

I can give you a whole lot of quotes about not comparing your middle to someone else’s end and the like, but the realty is there are a lot of terrific artists who participate in these things and we are our own worst critics.

Eventually you get over this sort of thing I think and develop a bit of a thicker skin making it easier to just join in for the fun and not worry too much about your perceived relative ability. But if that doesn’t describe you at the moment, then think twice about joining in. We all go through these phases of doubt so figuring out how best to steer yourself through them is an important part of being a happy creator. There will be other challenges so it is not the end of the world if you decide this particular one is not for you right now.

Of course, the other thing that can be terribly disheartening is when you realise you have bitten off more than you can chew and you get behind.

If you were doing the challenge to build skills and confidence you may find the challenge becomes counterproductive and you feel worse than when you started.

How to choose an art challenge and make it work for you

What’s your motivation?

To my mind, perhaps the most important part of participating in an art challenge is figuring out your why.

What do you want to get out of taking part in the art challenge?

More skills, body of work, community/social aspect - habit building?

There are no wrong answers or reasons here. But it is important that you are clear about your motivation so that when you get tired somewhere in the middle there you can remind yourself why you are doing this and or evaluate whether participating is giving you what you were looking for.


Be realistic

It can be easier said than done, but it is important to be very realistic about how much time you actually have available for this project. This is also why I think it is important to figure out your motivation first so that you are very clear about the importance of the challenge relative to everything else you are currently committed to.

Once you are committed to a challenge, it can tend to take over your life… just saying.

If you have never done a challenge before, then I strongly recommend starting small. You want a low bar and easy win or else this ‘fun project’ becomes one giant feel bad.  

Committing to 365 daily sketches on instagram sounds good, but how will you feel on day 12?

Or when you go on holiday?

Or when you feel unwell?

Or if it’s your birthday? 

There are lots of ways to dip your toe in the water as it were. There are one-off challenges to participate in just to see how you find it such as Dena Tollefson’s Colour challenges. These are stand alone projects that just involve producing one piece of art in response to a prompt - in Dena’s case a colour prompt.

This was my contribution to the Green and Gold Challenge for instance. A relatively small commitment, and a wonderful supportive community. An excellent place to start if you are on Youtube and haven’t been part of a challenge before.

There are lots of others you will come across on social media such as Draw this in your Style, or Fairy Friday.

There are daily, weekly and monthly challenges. Check out Daily Paintworks to see a whole lot of artists committed to daily creating.

There are also some fairly long challenges that do have an end point - I like the idea of daily painting but it is the perpetuity that give me pause!

One such challenge is the 100day project. I started drawing my little mixed media ‘Grace Girls’ for a 100day project a few years ago and they really took on a life of their own.


You never know where a challenge might take you. Don’t be put off by the difficulties. The struggle is real for sure, just be realistic enough to set yourself up for success. 

Avoid Scope Creep

Another thing that tends to happen ever so easily is that your tiny project takes on a life of its own and grows larger than you initially realised. For example, let’s say you decide to do World Watercolour Month (like I just did!) and complete 31 paintings in 31 days. That in itself might be enough of a challenge. Then, brimming with enthusiasm for this endeavour you think to yourself, hmm why don’t I record those daily paintings and then I will be able to produce a daily video. …

Great idea…. Or is it? Now, not only do you have a painting to produce every day without fail for a month but you also have to record, edit and publish a video every day too. 

Doable? Of course. But suddenly your daily painting challenge just doubled or tripled the time commitment. If you are clear about exactly what you are getting into you can make a sensible decision for yourself.

Now as you may know, I did precisely this - you can check it out here. I agonised over whether or not to take on this challenge because I have had my fingers burned by this sort of scope creep before. In the end of course, I did jump in and I’m glad I did. But it did reaffirm for me that all that deliberation about taking on the project was terribly valid!

Know Thyself

Big group art challenges can be motivating and confidence building because most of them have a very positive vibe and supportive community. However, you will probably be looking at a broad variety of other people’s work and it is possible that you will come across other artists contributions that you consider staggeringly better than your own. 

Be honest with yourself - if you know that comparison is going to get to you then perhaps avoiding putting yourself in that position for now is best. It doesn't mean you can't do a challenge - there is nothing stopping you making your own challenge. 

Developing your own personal projects is a great way to get started. You don’t even have to share it anywhere if you don’t want to. Of course the trade off there is that sharing it somewhere keeps you accountable and can help motivate you to finish the challenge. And obviously, keep it private by not posting if you dont feel confident about that.

But people are generally more supportive than you might think.

I promise.

Need some help with your first or next painting project?

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